Sheinman



Dec. 26, 1950 H. SHEINMAN 2,535,238

CURTAIN CONSTRUCTION Filed Feb. 12,1947 2 Sheets-Sheet 1 4 24 2 FIG! 'l I I /9-'": /9 I I I I l i I 28 20b 4 I l: I I: I 3

Zhmentor HARRY SHE/NMA/V (Ittorneg Dec. 26, 1950 H. SHEINMAN CURTAIN CONSTRUCTION 2 Sheets-Sheet 2 Filed Feb. 12, 1947 Q it u u u Ihwentor HARRY SHE/NMAN (Ittorneg Patented Dec. 26, 1950 UNITED STATES PATENT OFF-ICE CASTOR OIL-ORGANO SILICON BEACTION' PRODUCTS AND METHOD FOR THE PRO- DUCTION THEREOF Frank J. S'owa, rani'ord,!. J.

No Drawing. Application January." 1947 Serial No. 121,411

Claims. (0]. 26M) This invention relates to useful products obtained by the reaction of castor oil and various organosilicon compounds, and to a method for the production thereof.

The objects of this invention are briefly as follows:

1. To prepare by the reaction of castor oil and certain classes of organosilicon compounds materials which are useful as lubricants, plasticizradical, X is a halogen atom or an alkoxy group,

y is one or two, and z is two or three, the fourth silicon valence, if not occupied by R or X, being occupied by a hydrogen atom.

p The following examples-illustrate the. method for the preparation of several of the reaction products of this invention.

Example I y 466.5 gms. of castor oil and 117.1 sins. of

monoamyl triethoxysilane were heated to 160 6..

and the heating was thereafter continued for about six hours. During this time. ethyl alcohol was formed and the temperature of the reaction mixture gradually dropped to 130 C. The

contents of the flask were then cooled and again heated under reduced pressure; during which heating under reduced pressure 65 ms. of ethyl alcohol were collected in a Dry-Ice trap. The residue remaining in the reaction flask was a viscous oil which had good lubricating properties by itself or in conjunction with various solvents.

' Example II 59 gms. of diethyl diethoxysilane and 732.8 gms. of castor oil were placed in a three-necked flask which was fitted with a thermometer, a

stirrer, a fractionating column, a take-oif head. and a reflux condenser. The flask and its con-- tents were then heated to 170-174" C., and the vapor temperature rose to 85 C. when ethyl alcohol was liberated from the reaction mixture. When the maximum amount of alcohol had been liberated, the vapor temperature remained at 79 C. The flask was then cooled. and the alcohol was removed under a vacuum. The product remaining in the flask weighed 755 2 (theoretical yield. 762 ms), and had a Gardner-Holdt viscosity of 7.56 poises at 25 C. and a viscosity index of 110. Th reaction product was compatible in all proportions with nitrocellulose and ethylcellulose solutions, and was a uiselgul plasticizer for those film-forming mater a Example III 59 ms. of diethyl diethoxysilane and 366.4 sins. of castor oil were placed in the same apparatus as was described in Example II, except that no fractionating column was used. The flask and its contents were heated to -175 0., and the vapor temperature dropped from 140 to 110 C. after a reflux period of 13 hours. After the ethyl alcohol had been removed by means of a vacuum, 385 gms. of material (theoretical yield, 395 gins.) remained in the flask. 'The reaction product had a Gardner-Holdt viscosity of 3.1 poises at 25 C. and a viscosity index of 122.7. This material, too, was compatible with ethylcellulose and nitrocellulose solutions. and was a useful plasticizer for those film-forming materials.

E'zample IV 59 gms. of diethyl'diethoxysilane and 244mm. of castor oil were placedin the apparatus described in Example II. The temperature of the ingredients in the flask was raised to C., and the vapor temperature during refluxing dropped from 100 to 80 C.v After cooling, the ethyl alcohol was removed by means of a vacuum. 260 gms. of product (theoretical, 273 gms.)

remained in the reaction flask. The product had a Gardner- Holdt viscosity of 3.2 poises at 25 C. and had a viscosity index of 127.4. The

material was compatible with nitrocellulose and ethylcellulose, and was a useful plasticizer for those materials.

Example V 117 ms. of monoamyl triethoxysilane and 549 gms. of castor oil were charged into the appa- Example VI three-necked flask which was fitted with a dropping funnel, a stirrer, a condenser, and a receiver. From the dropping funnel 17.8 gms. of diethyl dichloro silane was added sfowly to the castor oil at room temperature. After the addition of the silane had been completed, the temperature of the reaction mixture was slowly raised to 100 C. The time required for the addition of the silane and the subsequent heating of the reaction mixture was 11 hours, during which period of time the entire apparatus was operated under a slight vacuum and the exhausted gases were passed through a trap containing aqueous caustic soda. The oily reaction mixture remaining in the flask was acidic, and therefore in order to neutralize it the mixture was heated at 100 C. in contact with an excess of lithium carbonate until the product had been made neutral. The excess lithium carbonate and lithium chloride was then separated from the product by means of filtration to yield 520 gms. of material having a Gardner- Holdt viscosity at 25 C. of 11.9 poises. The reaction product was compatible with nitrocellulose and ethyl cellulose solutions, and was a useful plasticizer for these film formers.

' Example VI! 240 gms. oi monolauryl triethoxy silane and 825 gms. of castor oil were charged into a threenecked flask which was fitted with a stirrer, a 12-inch fractionating column, a take-off head, and a condenser. The mixture was heated with stirring and ethyl alcohol was gradually distilled ofi while the temperature of the mixture in the flask was not permitted to rise above 180 C. Ihe final traces of alcohol were then removed by the application of a vacuum. This procedure required 12 hours, and yielded 1011 gms. of product having a Gardner-Holdt viscosity at 26 C. of 11.3-poises. The material thus produced was usefull as a lubricant and also as a piasticizer for nitrocellulose and ethyl cellulose.

Each of the products prepared in Examples II-Vll was oily in character and was useful as a lubricant. These materials were valuable p1as= ticizers for nitrocellulose because of their high viscosity index, as indicated in the table below:

of the organosilicon compound employed as a reactant, the reaction may be carried out at atmospheric pressure, as shown in the examples, or at supe'ratmospheric pressure when it is de- 5 sired to limit the escape of an organosilicon compound of high vapor pressure from the reaction zone before the reaction has been completed. Furthermore, depending upon the particular organosilicon compound selected, the reaction may initiate spontaneously, or it may be initiated by means of mild heating, as is shown in the examples.

.For the organosilicon compounds used as a reactant in the examples, there may be substi- 5 tuted any compound of the class RySiXz, in which R is an alkyl radical, X is a halogen (e. g., fluorine, chlorine, or bromine) or an OR group (1% being an alkyl radical), y is one or two, and z is two or three, the remainder of the four silicon valences, if any, being occupied by hydrogen.

Thus, among the organosilicon compounds which may suitably be employed as a reactant are n-amyl clichlorsilicane, n-amyl dimethoxysilicane, n-amyl trichlorosilicane, di-n-amyl dichlor- 5 silicane, n-amyl triethoxy silicane, methyl trifiuorosilane, dimethyl difluorosilane, ethyl tribromosilane, diethyl dibromosilane, n-propyl tri-nbutoxysiane, di-n-propyl di-n-butoxysilane, etc. Preferably, R is an alkyl group having from one to five carbon atoms, such as'the methyl, ethyl,

n-propyl, i-propyl, n-butyl, n-amyl, etc. radicals, and R is the methyl or ethyl group. Preferably, also, 0.3-1.0 equivalents of the organosilicon com pound are employed per equiva ent of caster oil,

based upon the hydroxyl content thereof.

because of their stability and viscosity index.

which is particularly h'gh considering the of silicon in the products. All the products, in:- t ermore, are characterized by their substantie y oily nature, and this property. combined with the property of highvisccsity index, makes Viscosity in Centistolu" Ex. qnane M lar Rati Index No. C. 0. Silanr (Viscosity) 25 C. 17 C. 97 C II Dlethyl diethoxy... l 0. 5 67 .4 327.1 27. 19 110 III do l l 239. 5 140.1 16. 46 122. 7 IV. .W-JIO l I l. 5 308. 2 146. 9 17. 96 127. 4 Monoam 'l triethoxy l 2 l 3072 1493 137 132 VI "Dicthyl dichloro 1 :1. 5 1415 607. 2 51. 22 118. 9 VII Monolnurl triethoxy l l 1359 605 48.1 119 Castor Oil (C. O.) l :0 756 388 22. 57 72.3

The foregoing examples illustrate the method of this invention for the preparation of castor oil-organosilicon reaction products by contacting (35 the halogen-substituted silicanes and the castor oil is a condensation with the loss of hydrogen halide, while the reaction between the alko ysubstituted silicane and the caster 01 is a condensation with the loss of alcohol. Depending valuable lubricants. The reaction products dis closed herein, when oflow viscosity, may be used as such as hydraulic fluids; when of high vsccsity they may be used as hydraulic fluids when in solar-- tion in various solvents, such as acetone, methyl ethyl ketone, fusel oil, isobutyl alcohol, and the m-onobutyl ether of ethylene glycol.

This application is a continuation-in-part of my abandoned application Serial No. 337,833, filed May 29, 1940, and entitled Silicon Compounds and Method of Making the Same.

I claim: W

9011 e pa r v p r pre e cha acteris ics ,1, a reaction product of castor oil and an or 

